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Preparation method for 2,9-dibutyl sebacate

A technology of butyl sebacic acid and dimethyl n-butyl malonate, applied in the chemical field, can solve the problems of principle toxicity, difficult separation, complicated process, etc., and achieves good product color, high reaction yield and simple operation. Effect

Inactive Publication Date: 2015-11-11
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Aiming at the above-mentioned technical problems in the prior art, the invention provides a kind of preparation method of 2,9-dibutyl sebacic acid, the preparation method of described this 2,9-dibutyl sebacic acid solves the problem of The method for preparing 2,9-dibutyl sebacic acid in the prior art is complicated in process, difficult in separation, and the principle used in the process is more toxic.

Method used

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  • Preparation method for 2,9-dibutyl sebacate

Examples

Experimental program
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Effect test

Embodiment 1

[0026] Add 94 g (0.5 mol) of commercially available butyl dimethyl malonate and 150 mL of anhydrous diethyl ether into a three-neck flask equipped with a thermometer, a condenser, and a drying tube, and start stirring. Cut 11.5g (0.5mol) of the weighed sodium block into relatively small sodium particles in n-hexane, add it to the above-mentioned reaction solution in batches within two hours, and continue to heat and reflux for 2 hours until the reaction system The sodium particles in it disappear. Then, while heating and stirring, slowly add 1,6-dibromohexane 122g (0.5mol) 150mL anhydrous ether solution dropwise to the reaction solution, control the rate of addition, so that the 1,6-dibromohexane solution is in 3 The addition was complete within hours and the reaction was heated to reflux overnight.

[0027] Heating was stopped, and the reaction system was cooled to room temperature. Add appropriate amount of dilute hydrochloric acid to the system at room temperature to make...

Embodiment 2

[0029] 91.7 g (0.2 mol) of the above-mentioned tetraester and 250 mL of methanol were successively added into a 1 L three-necked flask equipped with a thermometer and a condenser, and stirring was started, and 34 g (0.6 mol) of potassium hydroxide solution was added. The oil bath was heated to reflux, and the heating was stopped after 14 hours, and the reaction system was cooled to room temperature. Add 50mL of concentrated hydrochloric acid dropwise to the system under an ice-water bath until the solution is acidic. At this time, a large amount of white solids will be found to separate out. Filter and wash the filter cake with water to neutrality, then dry. The dried solid product is 71.6g. The rate is 89%.

Embodiment 3

[0031] Return the solid 8.04g (20mmol) obtained in Example 2 to the reactor, heat up while stirring, and when the temperature is raised to partially dissolve the solid, maintain this temperature and stir to completely liquefy the solid, and continue decarboxylation at this temperature React until the reaction is essentially complete (approximately 4-5 hours are required). Cool to room temperature. After dissolving in ethyl acetate, pure ethyl acetate was used as eluent to separate by column chromatography to obtain pure 2,9-dibutyl sebacic acid as a white solid, weighing 5.72 g, with a yield of 91%.

[0032] 1 HNMR (400MHz, d- DMSO): δ0.82(m,6H),1.19(m,16H),1.35(m,4H),1.43(m,4H),2.13-2.150.93(t,J=4Hz,2H),11.9(s ,2H).

[0033] 13 CNMR (400MHz, d- DMSO): δ177.39, 45.33, 32.34, 32.06, 29.58, 29.33, 27.30, 22.54, 14.21

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Abstract

The invention provides a preparation method for 2,9-dibutyl sebacate. The preparation method comprises the following steps: dissolving butyldimethyl malonate in a solvent, then adding chopped sodium particles in batches, continuing stirring and carrying out a reaction under a heating condition after completion of addition, and then adding a dibromination reagent drop by drop so as to obtain 2,9-dibutyltetramethyl tetracaprate; adding strong aqueous alkali into 2,9-dibutyltetramethyl tetracaprate and carrying out a reflux reaction in a solvent so as to obtain 2,9-dibutyl tetracapric acid; and adding a high boiling solvent into 2,9-dibutyl tetracapric acid and carrying out a reflux reaction in a solvent for a certain period of time so as to obtain 2,9-dibutyl sebacate. The preparation method provided by the invention has the advantages of low cost, simple operation, easy realization of reaction conditions, high reaction yield, good product color and convenience in industrialization production.

Description

technical field [0001] The invention belongs to the field of chemical industry, in particular to a kind of 2,9-dibutyl sebacic acid, specifically a kind of preparation method of 2,9-dibutyl sebacic acid. Background technique [0002] 2,9-Dibutyl sebacic acid (I) is a branched dicarboxylic acid, which is an important additive in the electrolyte of aluminum electrolytic capacitors. [0003] [0004] At present, the electrolyte of aluminum electrolytic capacitors generally uses ethylene glycol as the solvent, and organic carboxylic acids such as adipic acid, azelaic acid, sebacic acid and their corresponding ammonium salts as the solute. The electrolyte composed of such solutes can also maintain good dielectric properties and stability of the film layer in an environment above 100 ° C, so it has been used in high-voltage capacitors for a long time. However, because the aluminum electrolytic capacitor made of the above electrolyte is prone to esterification reaction at high ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C55/02C07C51/38
CPCC07C51/38C07C51/09C07C67/343
Inventor 欧文华
Owner SHANGHAI INST OF TECH
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